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60-32-2 molecular structure
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6-aminohexanoic acid

ChemBase ID: 395
Molecular Formular: C6H13NO2
Molecular Mass: 131.17292
Monoisotopic Mass: 131.09462866
SMILES and InChIs

SMILES:
OC(=O)CCCCCN
Canonical SMILES:
NCCCCCC(=O)O
InChI:
InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)
InChIKey:
SLXKOJJOQWFEFD-UHFFFAOYSA-N

Cite this record

CBID:395 http://www.chembase.cn/molecule-395.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
6-aminohexanoic acid
IUPAC Traditional name
6-amino hexanoic acid
aminocaproic acid
Brand Name
Acepramin
Acepramine
Afibrin
Amicar
Amikar
Aminokapron
Atsemin
Caplamin
Capracid
Capramol
Capranol
Caprocid
Caprolisin
EACA
EACS
Epsamon
Epsicapron
Epsikapron
Epsilcapramin
Epsilcapramine
Hemocaprol
Hemopar
Hepin
Ipsilon
Respramin
Synonyms
Aminocaproate
ACS
Aminocaproic
aminocaproic acid
ε-amino caproic acid
ε-Ahx
6-aminohexanoic acid
E-aminocaproic acid
Aminocaproic Acid
6-Amino-n-hexanoic acid
6-Aminocaproic acid
EACA
ε-AMINO-n-CAPROIC ACID
ε-Aminocaproic acid
6-Aminohexanoic acid solution
Additive Screening Solution 32/Fluka kit no 78374
6-Aminohexanoic acid
A 14719
Acepramin
Acepramine
Acikaprin
Afibrin
Amikar
Aminokapron
CL 10304
CY 116
Caplamin
Capramol
Caprocid
Caprolisin
EACS
Epsamon
Epsicapron
Epsikapron
Epsilcapramin
Epsilon S
Hemocaprol
Hemopar
Hepin
Ipsilon
NSC 212532
NSC 26154
NSC 400230
Respramin
ε-Amino-n-caproic Acid
ε-Amino-n-hexanoic Acid
ε-Aminohexanoic Acid
ε-Leucine
ε-Norleucine
ω-Aminocaproic Acid
ω-Aminohexanoic Acid
6-Aminohexanoic Acid
6-Aminocaproic acid
Amicar
6-Amino Hexanoic Acid
epsilon-Aminocaproic acid
6-氨基己酸
6-氨己酸
ε-氨基己酸
6-氨己酸
6-氨基己酸
CAS Number
60-32-2
EC Number
200-469-3
MDL Number
MFCD00008238
Beilstein Number
906872
Merck Index
14432
PubChem SID
160963858
24890662
46508972
46506934
24278238
PubChem CID
564

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.72614  H Acceptors
H Donor LogD (pH = 5.5) -2.050338 
LogD (pH = 7.4) -1.9963912  Log P -1.9971552 
Molar Refractivity 34.6598 cm3 Polarizability 13.835553 Å3
Polar Surface Area 63.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -2.69  LOG S -0.46 
Solubility (Water) 4.52e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
5.05E+005 mg/L expand Show data source
H2O: soluble0.5 M, clear expand Show data source
H2O: soluble50 mg/mL expand Show data source
Water expand Show data source
Apperance
white powder expand Show data source
White Solid expand Show data source
Melting Point
203-205°C expand Show data source
204-206 expand Show data source
207-209 °C (dec.)(lit.) expand Show data source
210-212°C expand Show data source
Density
1.03 g/mL at 20 °C expand Show data source
Hydrophobicity(logP)
0 expand Show data source
-2.235 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
MO6300000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319 expand Show data source
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... PLG(5340) expand Show data source
human ... PLG(5340)rat ... Ppm1a(24666) expand Show data source
Purity
≥98.5% (NT) expand Show data source
≥99% expand Show data source
≥99% (titration) expand Show data source
≥99.0% g/mL expand Show data source
95% expand Show data source
98% expand Show data source
99% expand Show data source
Concentration
1 M expand Show data source
Grade
puriss. expand Show data source
SAJ special grade expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Packaging
vial of 200 mg expand Show data source
Ignition Residue
≤0.1% expand Show data source
Impurities
≤0.005% Phosphorus (P) expand Show data source
≤0.1% Insoluble matter expand Show data source
Cation Traces
Al: ≤0.0005% expand Show data source
Ca: ≤0.005% expand Show data source
Cu: ≤0.0005% expand Show data source
Fe: ≤0.0005% expand Show data source
K: ≤0.005% expand Show data source
Mg: ≤0.001% expand Show data source
Na: ≤0.02% expand Show data source
NH4+: ≤0.05% expand Show data source
Pb: ≤0.001% expand Show data source
Zn: ≤0.0005% expand Show data source
Antion Traces
chloride (Cl-): ≤0.05% expand Show data source
sulfate (SO42-): ≤0.05% expand Show data source
Linear Formula
H2N(CH2)5CO2H expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02101645 external link
Crystalline
A plasmin inhibitor.
DrugBank - DB00513 external link
Item Information
Drug Groups approved; investigational
Description An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. [PubChem]
Indication For use in the treatment of excessive postoperative bleeding.
Pharmacology Aminocaproic acid works as an antifibrinolytic. It is a derivative of the amino acid lysine. The fibrinolysis-inhibitory effects of aminocaproic acid appear to be exerted principally via inhibition of plasminogen activators and to a lesser degree through antiplasmin activity. Aminocaproic acid may be a possible prophylactic for vascular disease, as it may prevent formation of lipoprotein (a), a risk factor for vascular disease.
Toxicity A few cases of acute overdosage with intravenous administration have been reported. The effects have ranged from no reaction to transient hypotension to severe acute renal failure leading to death. The intravenous and oral LD50 were 3.0 and 12.0 g/kg respectively in the mouse and 3.2 and 16.4 g/kg respectively in the rat. An intravenous infusion dose of 2.3 g/kg was lethal in the dog.
Affected Organisms
Humans and other mammals
Biotransformation Sixty-five percent of the dose is recovered in the urine as unchanged drug and 11% of the dose appears as the metabolite adipic acid.
Absorption Absorbed rapidly following oral administration. In adults, oral absorption appears to be a zero-order process with an absorption rate of 5.2 g/hr. The mean lag time in absorption is 10 minutes. After a single oral dose of 5 g, absorption was complete (F=1).
Half Life The terminal elimination half-life is approximately 2 hours.
Elimination Renal excretion is the primary route of elimination, whether aminocaproic acid is administered orally or intravenously.
Distribution * 23.1 ± 6.6 L
Clearance * 169 mL/min
External Links
Wikipedia
RxList
Drugs.com
DrugBank - DB04134 external link
Item Information
Drug Groups experimental
Description An antifibrinolytic agent that acts by inhibiting plasminogen activators which have fibrinolytic properties. [PubChem]
Selleck Chemicals - S1671 external link
Research Area: Cardiovascular Disease
Biological Activity:
Aminocaproic acid(Amicar) is a derivative and analogue of the amino acid lysine, which makes it an effective inhibitor for enzymes that binds particular residue. Such enzymes include proteolytic enzymes like plasmin, the enzyme is responsible for fibrinolysis. For this reason it is effective in treatment of certain bleeding disorders, especially fibrogenemia, and is marketed as Amicar. Aminocaproic acid is also an intermediate in the polymerization of Nylon-6, where it is formed by ring-opening hydrolysis of caprolactam. [1]
Sigma Aldrich - A2504 external link
包装
1 kg in poly bottle
25, 100, 500 g in poly bottle
5 kg in poly drum
Application
EACA is directly soluble in water at 25 mg/ml. As an inhibitor of plasmin it is has been utilized in the clotting buffer for fibrinogen assays. This buffer is 10 mM potassium and sodium phosphate, pH 6.4, with 0.20 g CaCl2, 5 g 6-Aminohexanoic acid, 1 g sodium azide, and 9 g NaCl in 1 liter. The buffer is stable indefinitely at room temperature.
Biochem/physiol Actions
EACA is reported to inhibit chymotrypsin, Factor VIIa, lysine carbo-xy-peptidase, plasmin, and plasminogen activator.
赖氨酸类似物。促进纤溶酶快速解离,从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。据报告,EACA 可抑制纤溶酶原结合至活化的血小板。早期报告表明,EACA 可抑制补体系统第一组分的活化。结合并灭活羧肽酶 B。
Sigma Aldrich - A7824 external link
Biochem/physiol Actions
赖氨酸类似物。促进纤溶酶快速解离,从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。1,2据报告,EACA 可抑制纤溶酶原结合至活化的血小板。3早期报告表明,EACA 可抑制补体系统第一组分的活化。4结合并灭活羧肽酶 B。5
Sigma Aldrich - A9812 external link
包装
棕色螺纹盖样品瓶包装
Biochem/physiol Actions
赖氨酸类似物。促进纤溶酶快速解离,从而抑制纤溶酶原的活化以及后续的纤维蛋白溶解。1,2据报告,EACA 可抑制纤溶酶原结合至活化的血小板。3早期报告表明,EACA 可抑制补体系统第一组分的活化。4结合并灭活羧肽酶 B。5
Sigma Aldrich - A44606 external link
Application
Hemostat.2,6 Used as a lysine analogue to characterize binding sites in plasminogen.7,8
Biochem/physiol Actions
Lysine analog. Promotes rapid dissociation of plasmin, thereby inhibiting the activation of plasminogen and subsequent fibrinolysis.1,2 Reported to inhibit plasminogen binding to activated platelets.3 An early report indicated that it inhibits the activation of the first component of the complement system.4 Binds and inactivates Carboxypeptidase B.5
Sigma Aldrich - 07260 external link
Other Notes
Improves solubilization of membrane proteins in electrophoresis6
Biochem/physiol Actions
Lysine analog. Promotes rapid dissociation of plasmin, thereby inhibiting the activation of plasminogen and subsequent fibrinolysis.1,2 Reported to inhibit plasminogen binding to activated platelets.3 An early report indicated that it inhibits the activation of the first component of the complement system.4 Binds and inactivates Carboxypeptidase B.5
Sigma Aldrich - 01-3540 external link
Biochem/physiol Actions
Lysine analog. Promotes rapid dissociation of plasmin, thereby inhibiting the activation of plasminogen and subsequent fibrinolysis.1,2 Reported to inhibit plasminogen binding to activated platelets.3 An early report indicated that it inhibits the activation of the first component of the complement system.4 Binds and inactivates Carboxypeptidase B.5
Toronto Research Chemicals - A609985 external link
6-Aminohexanoic Acid is a reagent commonly used for the extraction of aldehydes from reaction mixtures. 6-Aminohexanoic Acid has also been shown to improve solubilization of membrane proteins in electrophoresis. Studies suggest that 6-Aminohexanoic Acid i

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Steffen, L.W., and Steffen, B.W., Clin. Chem. , 22 : 381, (1976).
  • • http://en.wikipedia.org/wiki/Aminocaproic_acid
  • • Ohta ,S. et al.: Chem. Pharm. Bull., 28, 1917 (1980)
  • • Shagger, H. et al.: Anal. Biochem., 199, 223 (1980)
  • • Soter, N.A. et al.: J. Immunol., 114, 928 (1980)
  • • Has been recommended as a reagent for the extraction of aldehydes from reaction mixtures, giving better recovery than bisulfite: Chem. Pharm. Bull., 28, 1917 (1980).
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PATENTS

PATENTS

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